This invention pertains to cyclic amino compounds having antidepressant and other psychotropic, bio-affecting properties and to their preparation and use. In some preferred embodiments, the invention is concerned with 1,3-disubstituted pyrrolidine, 1,4-disubstituted piperidine, or 1,4-disubstituted hexahydroazepine derivatives wherein the 3- or 4-substituent is benzyl, substituted benzyl, or substituted indolyl, and the 1-substituent is a 1-aryl-pyrrolidin-3yl, 1-aryl-piperidin-4-yl, or a 1-aryl-hexahydroazepin-4-yl moiety. These compounds and others structurally related thereto possess a unique serotonergic profile that makes them useful in the treatment of depression.
Mattson and Catt disclosed a series of piperazinyl- and piperidinyl-cyclohexanols characterized by structural formula A as anxiolytic agents in U.S. Pat. No. 5,387,593. ##STR2##
Mattson and Catt also disclosed a series of cyclohexylpiperazines and -piperidines characterized by structural formula B as antiischemic agents in U.S. Pat. No. 5,352,678. ##STR3##
Mattson and Catt have also disclosed a series of piperazinyl- and piperidinyl-cyclohexenes and cyclohexanes characterized by structural formula C for treating ischemia-induced brain disorders in Eur. Pat. Appl., 560669, Sep. 15, 1993. ##STR4##
Scherer, et al. have disclosed the synthesis of some piperidinyl-piperidines, formula D, as as fluorescent probes (Recl. Trav. Chim. Pays-Bas, 112(10), 535-48, 1993). ##STR5##
Eldred, et al. disclosed a series of antithrombotic agents characterized by the formula E in Journal of Medicinal Chemistry, Vol 37, pp 3882-5, 1994. ##STR6##
Caprathe, et al. disclosed a series of piperazinyl-cyclohexanol compounds characterized by structural formula F in U.S. Pat. No. 4,957,921. Formula F is: ##STR7##
Caprathe, et al. disclosed a series of piperazinyl-cyclohexene compounds characterized by structural formula G in U.S. Pat. No. 4,975,445. Formula G is: ##STR8##
Smith, et al. in U.S. Pat. No. 4,954,502 disclosed a series of compounds of structural formula H having antidepressant properties. In these compounds A was, inter alia, a 5 to 7 carbon cycloalkanyl or cycloalkenyl ring. ##STR9##